4-Benzyloxy-2-hydroxybenzaldehyde → 5-Benzyloxy-2-hydroxymethylphenol

HRID 1891429Notes

Reaction equation

HRID 1891429 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:17])[C:12](=[CH:15][CH:16]=1)[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 251384215-Benzyloxy-2-hydroxymethylphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled suspension of 4-benzyloxy-2-hydroxybenzaldehyde (P1) (2.28 g, 10 mmol) in 10 mL of methanol was slowly added sodium borohydride (0.38 g, 10 mmol). After addition of sodium borohydride, a clear solution was obtained. The reaction was stirred at 0° C. for 20 minutes followed by stirring at RT for 10 minutes. The solvent was evaporated under vacuum. To this solid residue was carefully added 0.1 N H2SO4 until the pH dropped to 6.5 with vigorous stirring. Additional water (ca. 100 mL) was added with continuous stirring which then caused the product to precipitate. The solid was filtered and copiously washed with water to remove all traces of acid (last wash pH≧7). The solid was immediately vacuum dried to obtain (1.75 g, 76%) of P2 as a white solid: mp 88-90° C.; TLC, Rb0.29, in hexanes:EtOAc (2:1); 1H NMR (600 MHz, DMSO-d6) δ, 9.36 (s, 1H, Ph-OH), 7.43-7.32 (m, 5H, C6H5), 7.13 (d, 1H, J=8.4 Hz, Ar—H6), 6.44-6.41 (m, 2H, Ar—H5/Ar—H3), 5.01 (s, 2H, PhCH2), 4.8 (t, 1H, CH2OH), 4.39 (s, 2H, OHCH2).

Workup

  1. customa clear solution was obtained
  2. stirringby stirring at RT for 10 minutes
  3. customThe solvent was evaporated under vacuum
  4. additiondropped to 6.5 with vigorous stirring
  5. additionAdditional water (ca. 100 mL) was added
  6. stirringwith continuous stirring which
  7. customto precipitate
  8. filtrationThe solid was filtered
  9. washcopiously washed with water
  10. customto remove
  11. washall traces of acid (last wash pH≧7)
  12. customdried
  13. customto obtain (1.75 g, 76%) of P2 as a white solid

Sources & evidence

ORD record
ord-e91c17a56c8d439dab34a6dd0053334b
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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